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Hotels in Chestertown

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Top Rated Chestertown Hotels

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Luxury Hotels in Chestertown

    Driftwood Inn

    Driftwood Inn

    609 Washington Avenue, Chestertown, MD
    The price is $73 per night from Mar 9 to Mar 10
    1.3/5 (3 reviews)
    Driftwood Inn

Pet Friendly Chestertown Hotels

    Holiday Inn Express Hotel & Suites Chestertown

    Holiday Inn Express Hotel & Suites Chestertown

    150 Scheeler Road, Chestertown, MD
    The price is $89 per night from Apr 4 to Apr 5
    4.2/5Very Good! (24 reviews)
    Holiday Inn Express Hotel & Suites Chestertown
    Driftwood Inn

    Driftwood Inn

    609 Washington Avenue, Chestertown, MD
    The price is $73 per night from Mar 9 to Mar 10
    1.3/5 (3 reviews)
    Driftwood Inn
    Great Oak Manor

    Great Oak Manor

    10568 Cliff Rd, Chestertown, MD
    The price is $159 per night from Mar 9 to Mar 10
    Great Oak Manor

Where should you stay in Chestertown?

What are some of the best hotels for the budget traveler in Chestertown?

To find a good deal, consider these inexpensive hotels in Chestertown. Driftwood Inn is a 2-star property with free WiFi and free parking. Another option is Holiday Inn Express Hotel & Suites Chestertown, a 2.5-star hotel with free WiFi, free parking, and laundry facilities.

What are some favorite hotels in downtown Chestertown?

These are some of the most popular hotels in downtown Chestertown:

Though not in the heart of Chestertown, you may want to visit famous sights in the larger area like Chesapeake Bay Bridge and White Marsh Mall.

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